Drew Barrymore gets what others only dream about in this charming, fun comedy: a second chance to right the wrongs of high school! At 25, Josie Geller is the youngest copy editor at the Chicago Sun-Times, and the obvious choice to go undercover on a story about what the "cool kids" of high school are up to. A dorky teen dubbed "Grossie Josie" the first time around, this time Josie is required to make friends with the popular kids in order to deliver on her assignment. Unfortunately, now that Josie has come into her own as an intelligent young woman with a career and a brain in her head, those aren't the people she's interested in; as she begins to develop feelings for a teacher she's been ordered to portray badly, things start to get really complicated! Will Josie redeem herself from the mistakes she made in her high school years, or will she find herself repeating them all over again?